Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Windsor
Price found within the past 48 hours. Click for updated prices.
Where to stay in Windsor
Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Sandton
4 out of top 10 points of interest in this area
A noteworthy feature of Sandton is its popular shops. While you're in town, be sure to stop and check out Nelson Mandela Square and Sandton City Mall.
Rosebank
1 out of top 10 points of interest in this area
Rosebank is known for its ample dining options, and you can make a stop by Rosebank Mall and The Zone @ Rosebank Shopping Center while in the area.
O.R. Tambo
1 out of top 10 points of interest in this area
While visiting O.R. Tambo, you might make a stop by sights like International Terminal Duty Free Mall and Emperors Palace Casino.
Midrand
1 out of top 10 points of interest in this area
You'll enjoy the gardens and spas in Midrand. You might want to make time for a stop at Mall of Africa or Kyalami Racetrack.
Soweto
You'll enjoy the museums and churches in Soweto. You might want to make time for a stop at Maponya Mall or Mandela's House.
Windsor Hotel Deals
City Lodge Hotel at OR Tambo International Airport
Above Multi-Storey Parkade 2, Level 5 Kempton Park Gauteng
CA $204
CA $235 total
Nov 4 - Nov 5
includes taxes & fees
9/10 Wonderful! (2,090 reviews)
"Average in all respects. Was promised when booking that I could leave a case for a few days. Reconfirmed at check in. When came to leave in morning told that they could not keep case. Duty manager of no use at all. Couldn’t care less that promises had been made!,"
Reviewed on Oct 13, 2026
Sandton Sun & Towers
Cnr. Fith And Alice Streets Johannesburg Gauteng
Fully refundableReserve now, pay when you stay
CA $300
CA $345 total
Oct 27 - Oct 28
includes taxes & fees
Southern Sun O.R Tambo
Airport Grounds, Jones Road, / Kempton Park Gauteng
Fully refundableReserve now, pay when you stay
CA $149
CA $172 total
Nov 9 - Nov 10
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor vacation package cost?
Browse and book everything in one place with our Windsor vacation packages, which start from just CA $2,815. Select the hotels and flights that match your travel plans. Then, add on a few tours or experiences for an incredible getaway.
How do I get a cheap travel package to Windsor?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you dollars too. A Windsor vacation package makes it a cinch to arrange the ideal trip. With more than 550 airlines around the world to select from, finding flights that suit your schedule will be no sweat. Not only that, we have over 1,000,000 hotels globally to pick from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Windsor?
Stay where the action happens. Many travelers book hotels within easy reach of top attractions, such as Cresta Shopping Centre, Randpark Golf Club and Johannesburg Eye Hospital.
What are the top hotels in Windsor?
Get your trip off to a fantastic start by reserving a room at Isabel's Guesthouse. It's one of most sought-after hotels in Windsor. Another welcoming option is Khamanzi Lodge And Tours.
How far in advance should I book my Windsor vacation?
Search Expedia to compare international flights as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you've left things to the last minute, don't stress. The lowest prices to Windsor sometimes occur just weeks before departure.
What does an Expedia Windsor travel package include?
From airfares and hotels to car rentals, Expedia can help you create a Windsor package that's right for you. Heading away for a while? Look into a rental car, flight and hotel bundle. If your break is short, a hotel and airfare deal could be what you're after. Tours and activities can be added once you've made your booking. Our vacation packages make it a cinch to save and plan.
What should I know before booking a Windsor travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Simply choose your preferred air carrier and put together your ideal Windsor escape.
If I'm not able to travel, can I cancel my Windsor vacation package?
We totally get that life doesn't always go according to plan. If you've locked in a Windsor vacation package and have to amend or cancel it, we can help. We recommend taking a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.
Things to do
Johannesburg and Soweto: Half-Day Tour
CA $99
per adult
100% of travellers recommend
5 Day Luxury Kruger National Park Safari
CA $2,581
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.